Triethylamine → HCID 18710120, compound

HRID 278519Notes

Reaction equation

HRID 278519 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH:18](C)C)[NH:5][S:6]([NH:9][C@H:10]([C:14]([O:16][CH3:17])=[O:15])[CH:11](C)C)(=[O:8])=[O:7].N[C@H](C(OC)=O)C.Cl.S(N)(N)(=O)=O.CCN(CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH3:18])[NH:5][S:6]([NH:9][C@H:10]([C:14]([O:16][CH3:17])=[O:15])[CH3:11])(=[O:7])=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 82267SulfamideHCID 2733257Alanine methyl ester hydrochlorideHCID 12051191HCID 12051191, compound

Product 1

HCID 18710120HCID 18710120, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a procedure similar to the preparation of sulfamide (8b), H-Ala-OMe.HCl (2.18 g, 15.56 mmol) was subjected to sulfamide formation conditions (SO2Cl2, Et3N, CH2Cl2 0° C., room temperature, 2 hours). Flash chromatography (SiO2, Hexanes/EtOAc) yielded 617 mg (31%) of sulfamide (8a) as a white solid. mp=91-92° C.; TLC Rf=0.40 in (2:1 Hexanes/EtOAc); [α]25D=−75.8 (c=1.003, CHCl3); 1H NMR (CDCl3, 400 MHZ) δ5.24 (d, J=8.0 Hz, 2H), 4.09 (dq, J=7.3.7.3 Hz, 2H), 3.75 (s, 6H), 1.43 (d, J=7.2 Hz, 6H); 13C NMR (CDCl3, 100 MHZ) δ173.7,52.7,51.8,19.2; FTIR (neat) 3273, 1734, 1457, 1378, 1353, 1137 cm−1; HRMS (M+H)+ calculated for C8H17N2O6S 269.0807, found 269.0791.

Sources & evidence

ORD record
ord-8b98a19b181c4344a402b5de38f5c9e5
Source dataset
uspto-grants-2002_03
Patent number
US06359129B1

Reaction notes

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